This is part 2/2 of our second male chastity and femdom story. Read part one here.
I blinked my eyes a few times to help them adjust to the darkened room I was stood in. A number of red lights in the corners of the room illuminated the edges of the silhouette in front of me. I looked down at the metal bar and cuffs spreading my legs wide apart and the shiny black high heels that were fixed to my arched feet. My caged cock bulged in the lace underwear at the sight of my restrained body.
As I raised my chin the shadow of Mistress K suddenly disappeared, replaced by a latex clad goddess. With the click of a switch a spotlight came on above my head and I got a first glimpse of Mistress K's new purchases.
A transparent black latex skin tight catsuit covered Mistress's gorgeous body with a low cut front to show off her ample breasts, which were straining against the shiny material to get out. The key to my cock cage glinted in the light hanging from a silver chain around her neck. Cinching her waist was a black latex corset with 5 shiny buckles tightened across it, which pulled in her waist and focused my attention back to her bust. She'd expertly applied a luscious red lipstick to her lips and her eye make up was dark and fierce. Her shoulder length hair was tied back in a ponytail and adorning her pedicured feet were a pair of shiny black patent leather 7 inch heels with a steep arch.
My mouth dropped open and my cock squirmed in the steel metal cage between my forcibly spread legs.
“Correct response” Mistress said through a smile. “I've been wanting a new catsuit for a while and think this corset matches perfectly with it. I would thank you for paying for it but your money is my money, so I won't.
“You look incredible Mistress”. She immediately looked displeased and turned her back to me revealing a tight latex covered ass. I was in dreamland. This euphoric feeling quickly disappeared.
“I didn't tell you to talk, did I slave?” My legs suddenly turned to jelly and began to shake in my heels. The chains above my head restraining my hands rattled and the leather cuffs cut slightly into my wrists as they took some of my weight.
“I asked you a question,” she barked with her back still facing me. Mistress bent over slightly and the spotlight bounced perfectly off her tight arse. I was mesmerised and failed to notice what she was picking up off the table in front of her.
“Turn around and face the wall slave.”
I froze. How was I going to turn around with the heels on my feet and the spreader bar between my legs? I very slowly shuffled my feet in opposite directions and eventually managed to make a full turn so that I completed her request.
Heels clicked on the wooden floor behind me and a warm hand slid under my panties. Her sharp, polished nails dug into the skin around the cage and I cried out in pain. I focused on keeping my legs straight and not allowing my knees to buckle. Mistress seemed to sense this and dug her nails in harder. When that still didn't work she did the same with my exposed testicles hanging below the cage. This worked instantly and Mistress giggled when I scrambled to regain my balance.
Mistress squeezed my butt cheeks and pulled the panties up between them before ripping them down to my knees. She then walked over to the table behind me, slipped on a medical glove and something that sounded like more chains. Her heels once again clicked on the floor as she walked back towards me and I felt her lubed up gloved fingers slide between my cheeks and penetrate my puckered arsehole. I felt myself rolling onto the balls of my feet and started to enjoy her fingers grinding inside me. While the fingers on her right hand were inside me, her left hand gripped and turned the O-ring on the metal collar around my neck so that it was now facing backwards. Within moments something clicked and attached itself to the O-ring. A cold metal chain now trailed half way down my back.
The fingers in my ass rubbed my prostate and the metal cage obstructed any hope I had of getting an erection, but that wasn't going to stop me from cumming if Mistress carried on for too much longer. I moaned with pleasure and Mistress instinctively pulled her fingers out. Without hesitation she forced a cold metal anal hook into my ass and clicked the chain attached to the end of it into the chain hanging down my back. It was now fixed in place and leaning forwards at all pushed the plug deeper inside me.
“Legs straight, ass out” Mistress K ordered. I did as I was told and the plug filled me as the chain pulled. I looked down at the heels on my feet and realised I was starting to feel some pain.
“I've been thinking about this for a long time slave. The sissy girls under my control are showing excellent progress, so you'll have a lot of work to do to catch up. You'll do exactly what I tell you and you'll be taking my cock deep inside that filthy ass of yours like a good sissy by the end of this session. Is that what you want?”
“Yes please Mistress” I replied.
“It doesn't matter what you want. It's what I want and that's all that matters. Is that understood?”
“Yes Mistress.” I nodded my head and the chain attached to my collar pulled again giving me a small amount of pleasure with each tug.
“Good girl. A good sissy needs to learn to act like a lady and a whore. She must be attentive, dress to impress, do what she's told and take a cock like a slut in both holes. Today you're going to do all of these things and more. You're already dressed in beautiful lingerie, you have cute high heels on and my cock is locked away. This pleases me. I think I'll have you dress like this more often. Look at how much this pleases me slave.”
Mistress walked over and stood next to me, unzipped her catsuit in the crotch, reached down and slid her fingers between her legs. She then pulled them out and ran them over my lips, her pussy juices dripping into my mouth and filling me with excitement.
“See what you looking like this does to me? Now, let's get started with your training with some warming up. I'm going to flog, spank and cane that peachy arse. You're going to keep your legs straight, arse up and chest forwards. Failure will not be tolerated and you'll be punished accordingly if you don't do as you're told.”
As Mistress K walked towards the table of toys behind me I controlled my breathing and braced myself for the first impact. A warm open hand groped my shaking arse and Mistress quickly administered 5 hard spanks to each cheek. She gave me a few seconds before doing the same again, this time a little harder. I kept my composure and my legs remains straight throughout.
“Good girl. Let's step it up a little.”
The swish of a crop behind me made my balls contract and cock twitch. The first strike to my arse was mild, but with each additional strike the sting got worse. After around 25 strikes my legs wobbled and all I could think about was not slipping in my heels.
“Legs straight!” Mistress yelled as she struck me harder. My legs instinctively straightened and my mind snapped back into focus. The crop moved down my body and lightly tapped against the back of my thighs and calves. Being stood in the heels tightened the muscles in my legs and the pain from the crop was much more severe than usual.
Another 50 or so strikes later my mind was a mess. My knees were practically together and most of my weight was being taken by the cuffs around my wrists above me. Without realising it I'd started to drool a little with the spit dripping down my chin onto the floor. Mistress noticed this, got up close to my face and with her nose touching mine said “you'll clean that up later you filthy slut.” Her tone was harsh and I felt she was disappointed in me. I soon found out that she was.
After a few quick steps behind me Mistress K grabbed a short stinging leather flogger and flicked it at my smarting ass cheeks. I cried out in pain and gritted my teeth anticipating another impact.
“This is really going to hurt,” Mistress announced followed by cackling laughter. A bit gag was thrust into my mouth from behind. I quickly bit down just in time before she let it go. Instead of fixing the straps behind my head it was left to me to bite down and not let go.
The barrage of blows that came from the flogger against my back, arse and legs that came next made my head float. It felt like I was floating in the air and and each strike only helped to submerge my mind more. Suddenly it stopped.
Mistress K stepped backwards and admired the sissy shaking in front of her. Her arms stretched out above her head manacled in the chains and cuffs hanging from the ceiling, her convulsing legs spread apart by the bar fixed between them, the high heels forcing her legs to tense up and pert ass presenting itself to be used. With Mistress K admiring the state that she'd got her newly feminised slave into, the silence in the room was abruptly shattered. The bit gag her slave was biting down on during the flogging dropped onto the hard wooden floor. The latex clad goddess put one high heeled foot down in front of her and slowly stepped towards her slave after picking up a few items from the table next to her.
“Stage one is complete. Now, lets make you look like more lady like.”
A small black tube came into view below me and the top was removed. It was a light red lipstick. I lifted my head and turned towards her so that she could apply it to my quivering lips. She precisely placed the lipstick at the edge of my mouth and slid it across my lips. With my whole body still trembling I could tell by the agitated look on her face that it hadn't gone well.
“If you're going to constantly shake I can't make you look pretty,” she barked. “Luckily I have just the thing to make this easier for me.” Mistress thrust a red ball gag into my mouth and fixed it behind my head with the attached leather straps. She then perfectly applied the lipstick to my bottom lip using the round gag as a guide.
“There's still something missing” Mistress declared. She then pulled out what looked like a chunky pencil from her bust. “Close your eyes slave.” Eye liner was then drawn around the edges of both of my eyes.
“That's much better. Now you're finally starting to look like the sissy bitch I would be proud to parade in front of the other Mistresses. Maybe I'll invite them over to admire this beautiful transformation once your training is complete. You'd like that wouldn't you?”
I'd been used and abused by Mistress K's other Mistress friends a number of times, but never dressed in women's underwear or wearing make up. What would they think of me? It could be so embarrassing. This was a thrilling prospect.
A mirror was placed in front of my face and I got to see for the first time what I looked like.
“You look a mess. If you'd stayed still you'd have perfectly painted lips, but instead you forced me to gag you and make you look like a pathetic sissy girl rather than the high standard I'm used to. If you want to be a messy sissy I'll make sure that's exactly how you're treated.”
The cuffs attaching the spreader bar between my legs were removed, followed by the clips attached to the cuffs on my wrists. I managed to stand up straight and not collapse instantly to the floor. I started to get used to balancing in the high heels and the hook in my ass felt very much at home. I'd almost forgotten that Mistress's cock was locked away between my legs before it twitched at the sight of her dressed in the new latex catsuit and corset.
“Stand up straight and don't move until you're told to” Mistress commanded. As she disappeared out of the door to our bedroom my muscles relaxed and my legs almost cramped. They were aching and I desperately wanted to crumple to the floor. The door flung open and Mistress returned with a piece of equipment I'd not seen before. It appeared to be a short wooden post built into a metal stand. On the top and sides of the post were metal o-rings. She placed it on the wooden floor in front of me, clicked her fingers and pointed to the floor. As I sunk to the floor a flood of relief swept through my whole body. This feeling was short lived.
“Get on all floors, put your wrists next to the rings on the side of the post and your neck at the top.” My wrists were clipped to the sides of the post before the anal hook was removed from my ass. I immediately missed it pressing against my prostate and hoped that it would be replaced by Mistress's cock soon. My collar was turned around and the o-rings on the collar and post were clipped together. I was now kneeling down on the floor, my wrists and collar restrained to the post with my head just below Mistress's crotch. Finally, the red ball gag was removed from my mouth.
“Quite comfortable down there on your knees where you belong slut?” I eagerly nodded my head.
“It's time to put that ass and mouth to work.”
Towering above me Mistress K looked down at her new sissy and smirked with delight. She reached over to the table and walked behind me out of sight. When she returned a large purple strap-on cock hung between her legs attached to a heavy duty leather harness.
“Open that fuck hole mouth nice and wide sissy. You're going to learn to take all of this cock in your mouth and keep it there. Don't disappoint me.” As her knees bent slightly Mistress thrust her cock into my gaping mouth. My mouth engulfed her cock and I tried to pull my head back to get some rhythm going, but with my collar locked to the wooden post I couldn't move. Instead, she forced her cock down my throat and I gagged. I was instantly submerged in a swamp of helplessness and a single tear rolled down my cheek. With her quickening thrusts I naturally tried to pull my head back and close my mouth. When Mistress pulled out I gasped for air and the spit left on her purple dick strung out before falling on my face.
“It appears that you don't want my cock in your mouth slut. All of my sissies worship my cock and would be grateful to be in your position right now. Extreme measures are required.”
Out of the corner of my eye I noticed a shiny metal object being picked up from the table and it moved towards my head. A spider gag appeared in front of my face and I dutifully opened my mouth wide so that it could be attached. With my jaw stretched and a large unobstructed hole presented to use Mistress returned to the same position and held her cock in front of my face. A few red streaks covered the purple silicone dildo, which I realised were lipstick marks. My inner whore revelled in this.
“Resisting will only make it worse. Here's your punishment.” The purple cock thrust into my mouth once again, this time without any resistance. The metal gag between my teeth prevented me from biting down or swallowing, which caused a cascade of spit to run down my chin. The hard thrusts choked me and made my eyes fill with tears. Seeing these flow down my cheeks made Mistress K beam with joy and drove her to fuck my face even harder.
“You look so much prettier when you cry for me.” She fucked me breathless with her cock hitting the back of my throat with each thrust. With each thrust the cage between my legs rattled in my panties and the key around her neck bounced between her huge tits, both of which reminded me of the manhood I was losing. A hand locked onto the back of my head and pushed the cock deeper still. My gag reflex was being tested more than it ever had been before.
“Good girl. That's how a real sissy takes a cock. I think it's time for a reward.” With that, Mistress pulled out of my mouth and strutted behind me. She bent down, slid a condom onto her cock and forced my ass checks apart. She squirted some lube onto her rubber penis and stuffed it deep inside my gaping asshole. Her hands gripped onto my shoulders and she fucked my eager hole with long, deep thrusts.
The pool of spit forming on the floor in front of me was growing by the second. The hard fucking I was now experiencing sent constant shots of euphoria through my body and my cock twitched uncontrollably. My eyes started to roll into the back of my head but a sudden feeling snapped me back to attention. A sensation in my groin filled me with panic and I felt the urge to cum. With the spider gag in my mouth I couldn't speak or ask for permission. I screamed with pleasure and Mistress took that as a sign to penetrate me harder and faster still. A few seconds later my warm cum shot from Mistress's caged cock and began dripping through the panties onto the floor. Mistress quickly noticed.
“What is this?!” Mistress screamed as she stopped fucking me and reached round to feel the soaking wet panties between my legs.
“I didn't hear you ask for permission to cum slave. You better clean this up before I decide what to do with you.” My panties were ripped down from around my hips to my knees, pulled off my legs and over the heels that were still tied to my feet. With cum dripping from them onto the floor she walked next to me and stopped directly in front of my head. I noticed some of the warm cum had dripped onto her shiny black heels.
“Clean these with your tongue” was Mistress's instruction. The wet panties were stuffed into my gagged mouth and I swirled my willing tongue around the soft material. While I was swilling the panties in my mouth the cuffs were unlocked from the wooden post followed by the collar.
“You've made a mess of my shoes and the floor slave. Get down on your hands and lick it all clean.” As soon as I bent down to lick the cum from Mistress's heels a mouthful of spit covered her shoes. A strong hand grabbed my hair, untied the gag and formed my face towards the shoes. “Clean them. Now!” I lapped my tongue over her heeled foot till they sparkled once again. My head was then forced further down to the floor by a spiked heel on the back of my head.
“Don't let your tongue leave that floor till I tell you.” I slowly ran it along the wood floor capturing every drop of cum that had dropped from the panties.
“Keep your tongue on that floor and don't move” Mistress demanded once the last drop of cum had been licked clean. A cold metal anal plug slid into my raw arsehole and nestled tightly inside me.
“I was going to reward you for your excellent progress today, but failing to ask for permission to cum from my cock is a serious offence. Instead, you'll be wearing that plug in your arse to bed and you're not allowed to change out of your stockings, suspenders or heels for the next 24 hours. Is that understood?”
I nodded my head keeping my tongue firmly fixed to the floor so as not to incur any further punishments.
“Oh, one more thing. No orgasms for a month. We'll continue your training tomorrow. Now, go and clean yourself up. Your eye liner has run down your face and your lipstick has smeared all over you.” I slowly got to my feet and gingerly edged my way to the bathroom in my heels, taking small steps and trying not to fall over.
I looked at myself in the bathroom mirror. I was a complete mess. I felt incredible and couldn't wait for my next training session.
I hope you enjoyed the story. We'll do our best to get more stories posted onto the blog soon.
If you're looking to buy a male chastity device for your own play sessions you can get one on our store. Prices start from only £11.99 + P&P and we ship worldwide.
Please do post any comments or feedback in the comments below. We both love to read what you think about each and every story that we post.
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Chastity and FemDom Tasks List Story - Part 4
Chastity and FemDom Tasks List Story - Part 3
Comments
Mistress K:
@Mkbootlicker and @Louis
Thank you so much for your kind compliments. Slave D enjoys writing the stories on our blog and he has more coming soon for you. We’ll post links to all new stories as soon as they’re published on our Twitter account. If you don’t follow us already you can find us on Twitter @houseofdenial
Jan 22, 2021
Mkbootlicker:
Wow amazing story please keep doing them it was really good .very erotic and turned me on as im a closet sissy myself thank you xx
Jan 22, 2021
Louis:
Hello, I’m new to the world of domination and I have to admit this story is really hot. It’s well written and for the entire reading I was eager to learn more about this training session. From the beginning to the end I asked myself “What’s going to happen ?” and I have to admit, I’m not disappointed !
Sorry If there are some fault in this comment, I’m french and even if I speak english fluently I’m not good for writing it.
Have a wonderful day.
May 29, 2019
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